


open your heart to halloween chaos

by royalgreen (allyoop)



Series: Fictober 2020 [7]
Category: Critical Role (Web Series)
Genre: Alternate Universe - Canon Divergence, Bets & Wagers, Costume Parties & Masquerades, Costumes, Crushes, Cute, Fictober, First Kiss, Flirting, Fluff, Fluff and Humor, Friendship, Halloween, Halloween Costumes, Happy Ending, Humor, Jester threatens to eat her crown so you know this is Serious Business, M/M, Mutual Pining, Pining, Romantic Fluff, Team Bonding, Team as Family, Wingman Jester Lavorre
Language: English
Status: Completed
Published: 2020-10-31
Updated: 2020-10-31
Packaged: 2021-03-09 00:01:21
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,444
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27295333
Author URL: https://archiveofourown.org/users/allyoop/pseuds/royalgreen
Summary: Cats and bats, princes and pirates....this will be a Halloween to remember!It's Essek's first Halloween and Jester has chosen his costume. There is also a costume contest. There is also a lot of wine. This evening is going to go absolutely completely fine.
Relationships: Essek Thelyss/Caleb Widogast
Series: Fictober 2020 [7]
Series URL: https://archiveofourown.org/series/1954570
Comments: 12
Kudos: 148





	open your heart to halloween chaos

**Author's Note:**

> fictober prompts: "over dressed" and "nobody sees a thing"

“Jester, I still do not see the point of this.” Essek stated for the third time that day.

She stepped in front of the mirror, gently bumping him to step aside so she could check her outfit again. “Essek I told you, Halloween is the perfect excuse to wear costumes and get dressed up and eat pastries and sweets and-”

“Yes, but the _costume,_ ” he tugged at his own again, feeling more exposed than usual without his sweeping mantle. “Why not use a spell to disguise self? It seems much easier.”

She stuck out her tongue “It's all about the costume and having fun, not just doing a spell as a shortcut. I’m the queen tonight and I decree you shall have fun!” And she was queenly, literally. Jester was absolutely bedazzled in tiers of diamanté studded silk, silver lace, pearls, and all topped with a blindingly glittery tiara. She looked like a cross between a snowstorm and a cupcake, which was a compliment she would probably adore if Essek dared to say it aloud. Her costume made it all the more confusing to him though. Where Jester seemed to lean into the “more is more” approach and wear what would be overdressed for any other night, the outfit she had excitedly presented to Essek seemed to be missing quite a few layers.

Jester kept talking to him as he donned the outfit behind the privacy of the large screen in his bedroom. 

“My first idea was a cat, that’s a totally classic costume and should be really easy to find, even in this city. But then I thought it’d be too on the nose since you and Caleb are still doing your dumb who’s-gonna-confess-first game of chicken.” Essek had almost tripped into his screen at this point. She ignored his shocked noises of protest and kept going. “So I went with my second choice! It’s kind of in the same family, well not in the same animal family, actually I’m not sure about that. Is a bat related to a cat? Hey, Essek do you know?”

“Jester, can we backtrack to-”

“Maybe I’ll ask Caduceus later, he knows about stuff like this. Anyways, I thought bat because they can be cute and small, but also a little spooky and they usually hang out in the dark and wear black, and it just felt totally _you_.”

Essek stepped reluctantly out from behind the screen, wings held in his hand after unsuccessfully trying to wrestle the strappy thing onto himself. “Jester, while I do appreciate your help in the matter, I really don’t think…” He trailed off. There was a bright sparkling look in Jester’s eyes and Essek knew he had already lost. This was going to be his costume, and there was no going back.

Which is how Essek found himself in front of a mirror dressed in slinky black velvet, the deep color in high contrast next to Jester’s pearly queen. He was thankful the jacket had cutaway tails that swept down past his waist. These velvet trousers were rather snug, and Essek was unused to feeling so...on display. There really wasn’t much _battiness_ to it, other than the leather harness and attached wings. The straps buckled across his chest and shoulders, reminding Essek involuntarily of Caleb and his ubiquitous book harness, but this one was more intricate in how it criss-crossed. It all seemed rather unnecessary in Essek’s mind. The wings weren’t even that large, nor did they move. Although he could fix the latter though with a simple enough spell.

Jester was clapping with glee. “Oh my gosh Essek, why are you always hiding under cloaks and layers? You look amazing, like crazy super hot, Caleb is definitely going to lose his mind-”

“You keep mentioning him,” Essek tried to keep his voice steady. “But I really must make this clear. Caleb only thinks of me as a friend.”

“And what do you think of him, hmm?” She waggled her eyebrows even as he stayed silent. “Trust me, I know about this kind of stuff. He totally likes you. And you like him back, duh, that’s obvious-”

“Jester-” His face was starting to flush.

“But on the tiny, _tiny_ chance that I am wrong I promise to eat my tiara if he doesn’t make out with you by the end of the night.”

“What?!” Essek’s voice came out an octave too high. “No, don’t promise to do that, you can't possibly know for sure that Caleb, that he, and me-”

She threw her head back and laughed. “No, I’m gonna. I already said it and I don’t go backsies on promises!” She linked her arm into his. “Don’t worry Essek, that’s just how sure I am! And I really love this tiara, so I definitely do not want to eat it, blegh, it’s not even made of sugar or anything.”

Suddenly the pressure of the night seemed to increase beyond measure in Essek’s head. He was already feeling haplessly dragged into this social situation, a party for a holiday he knew nothing about, and now...well, he certainly didn’t want his friend to have to swallow down a piece of a costume.

The party was at the Xhorhaus but the familiar home was covered with an explosion of new decor. Ceilings were decked out in colorful streamers, walls covered with drawings of skulls smiling with two-tusk grins, and a plethora of glowing lights gently illuminated the space. Strings of lights ran from the large tree and towards the main building. It seemed like a lot of trouble for such a small party, the only attendees were the Nein and a few select friends, but it had been a difficult handful of months and Essek supposed everyone was eager for a party. 

Essek had teleported himself and Jester right to the Xhorhaus’s front yard, due to very much not wanting the general public to view his costume on the walk from his tower to the party. They caused a burst of mild chaos as Jester jumped out from the teleport shouting “I’m heeere!” and startling Fjord.

“Whoa-!” Fjord steadied the tray in his hand. It looked like he was on his way back inside to replenish some drinks. He did a double-take at Essek and then triple-taked at Jester. “Wow, Jester, you look… Well, I’m not really sure who you are supposed to be, but that sure is something.”

Jester did a twirl, showing off her full sparkly skirts to best effect. “Thank you! Gosh, I love Halloween, it’s such a good excuse to dress up.” She paused and squinted at Fjord. “Did you not get the very obvious invitation to wear a costume?”

Fjord pointed at his head where a tricorne hat perched. Other than the hat and a few pieces less of armor, he looked about the same as usual. “I’m a pirate.”

“No you’re not.” A voice came from around the corner and there stood Beau with a massive plumed hat, lavishly embroidered sleeveless coat, layers of gold chains and pendants, and tall black buckled boots. “ _I’m_ a pirate.” She grinned and clapped Fjord on the shoulder. 

He sighed. “I’m not really one for costumes-”

“Ohmygosh Beau, you look amazing!” Jester interrupted. “You look like a super rich fancy captain. Do you have a pirate name for tonight? Or should we just call you Captain Beau?”

“Ooh, I like the sound of that.” She smiled at Jester and turned to look at the tray in Fjord’s hands. “Let’s just bring the whole barrel of wine outside, I think most of the party is going to be drinking on the porch anyways.” 

“Is everyone else already here? Are the costumes amazing?” Jester asked.

“Yeah, most people are out back. And the costumes…” She chuckled. “I’ll let you be the judge of that. Oh, Caleb is here too.” She raised an eyebrow at Essek in a significant way.

Essek raised an eyebrow back, but in mild confusion. “I assumed he would be, as this is where you are currently residing.”

Beau shrugged and tugged on Fjord’s arm. “Come on, training time. Help me lug the wine barrels out here.”

Jester turned to waggle an eyebrow at Essek. He couldn’t help but think the Nein had a whole language among themselves of eyebrow communication. 

“Come on, let’s show off our costumes to the others! I can’t wait to see everyone’s faces.” Jester grabbed his hand and pulled him around to the back porch. Essek’s stomach flipped, that anxiety rising up again. He still couldn’t believe he had let Jester talk him into this whole evening.

The party noise was loudest in the backyard where most of the people were gathered. There were some groups in conversation, strums of a harp, the clinking sound of windchimes from the tree. Essek recognized most everyone, as expected, even if some were not as familiar. There was a small halfling child tugging on Veth and Yeza’s hands, which he could only assume was Veth’s son. The awkwardness of this environment seemed to increase tenfold. Continuing to gaze through the small group, he saw a few more strangers: a purple tiefling sitting on the grass beside Yasha and her harp, a freckled blonde woman with a faint glow above her head that he wasn’t sure was part of the costume or not. His eyes kept searching the crowd until, _ah_ , the familiar red hair he had been looking for. 

Essek would have bee-lined straight for Caleb without saying a word, but alas, he was still standing next to Jester.

“So sorry we’re late!” She skipped up to the crowd. “Hi everyone! Oh gosh, you all look so great! I love your costume, what are you supposed to be?” Jester immediately inserted herself into the circle of her friends, complimenting and conversing. 

Essek sighed. They had seen him, he was being waved over, there was no avoiding this. Although...it wasn’t too bad seeing Caleb’s eyes widen as he approached. Essek added a little swing to his step, for no particular reason at all. 

“Look, look, he’s a bat!” Jester took Essek’s hand again and pulled until he was forced to awkwardly spin in a circle to show off. “I picked everything out but doesn’t he look super great? Caleb, what do you think?”

Essek tried to give a confident look in his direction, but at best succeeded in a nervous smile. 

“It suits you, somehow.” Caleb’s eyes were still trailing slowly up and down, and Essek was reminded just how snugly the velvet clung. When was the last time he had worn anything but his flowing cloak or jacket ensemble in front of the Nein?

A wild idea struck him, Caleb’s lingering gaze giving him a burst of confidence. “Jester’s fashion choices are wonderful as always, however-” he turned so his back was facing Caleb and looked over his shoulder. “I find that all outfits are heightened with a bit of magic.” Essek did a little hand motion in the air and his leather wings flapped gently in an invisible wind.

“Oh, very nice.” Caduceus clapped a couple times. 

“Ja, like I said, it suits you.” Caleb was now smiling at Essek with a sparkle in his eye, and Essek felt suddenly like this party would be worth the trouble it cost.

“Are we still doing a costume contest?” Jester looked around excitedly. “I know I was the one that suggested the party, and also suggested the contest, and picked out the prize, but I’m so excited now that I’ve seen everyone’s costumes!!”

“How would it be fair, wouldn’t we all just vote for ourselves?” Veth approached, glancing over her shoulder as her son was climbing onto Yeza’s shoulders to try and catch some of the floating globules of light. “I mean, I’d definitely vote myself, I look great tonight. Plus, it’s family coordinated outfits and nothing is cuter than that.” She was wearing a blue and gold coat with a gun holster on her belt and round glasses on her nose, her son was carrying a crossbow and dressed in white leather, and her husband was inexplicably wearing a furry brown suit with matching headband ears.

Essek was deeply puzzled, he had no idea what the trio were supposed to be. “Are you also a pirate tonight?” He politely asked. Veth looked aghast.

“See I told you, no one knows who you are!” Beau was back with Fjord, two large wine barrels, and some precariously perched glasses. “I don’t think that book is very popular.”

“Yeza says Luc and all his friends are obsessed with it.” Veth shrugged. “It’s some wacky fiction, but I thought it made for some great costumes.”

“I have read it,” Caleb said, raising his hand slightly. “And you have captured the character details considerably well.”

“Fine, fine, I’ll give you points for book accuracy.” Beau gestured to her outfit. “But have you ever seen a better dressed Captain? Avantika, who?” She laughed at Fjord’s slightly stricken expression. “C’mon I bet even Essek would vote for me, right?”

“Well, I-” he was surprised to be included into this conversation. “You certainly are the best dressed pirate I’ve seen, on account of not appearing sunburned or salt-starched from some perilous sea adventure.”

Veth laughed. “Ha, he got you there Beau! You’re way too clean to be a real pirate.”

“Hey, the invite said ‘ _lavish_ costumes’, not ‘accurate’. Don’t make me take away the points I just gave you.”

“The points are made up and don’t matter!” Veth was still laughing.

“No fighting yet you guys!” Jester put her hands on her hips. “I also told people to be _creative_ or make their own costumes, remember? I think only Yasha followed that.” She gestured over to where Yasha was still playing her harp. Large paper petals were sticking out of a headband to give her the appearance of a large walking daisy.

“I will graciously give my made-up points to Yasha.” Veth grinned.

Beau rolled her eyes. “I was gonna give points for handmade anyways, so I guess Yasha gets double points.”

Fjord looked at Beau and frowned with confusion. “Wait, are you the judge of the contest? I thought Jester was.”

“Oh I still am, but we are _all_ kind of the judges. It’ll be a group vote, but I’m like the head judge. The judge queen.” She grinned. “Ooh, Empress Judge.”

“Uh oh, that’s too much power for one person.” Beau grinned. “Caduceus, you’re usually impartial, what do you say?”

“I definitely vote for myself.” He smiled placidly as everyone broke into giggles at the unexpected statement. “Hey now, this took me a long time to grow, and if you’re giving points for handmade and creativity…” He gestured at his outfit, which seemed to be truly alive. A mossy jacket was blooming with a pattern of luminescent mushrooms and little wildflowers. The jacket fell away into tendrils of vines and leaves, like a gentle skirt of a waterfall.

“You haven’t said _what_ you are though”

“I’m not really one thing, just like none of us are really one thing.”

Fjord tilted his head. “So you’re like the _concept_ of nature or something?”

“Yeah, that’s it exactly.”

“How did you get that on your first guess?” Veth looked surprised.

Fjord tapped his head with a grin. “Wildmother connection, you wouldn't understand.”

“Okay genius, try and guess Caleb’s then.”

The attention of the group shifted towards Caleb. If Essek didn’t recognize the origins of Veth’s outfit, he certainly hadn’t the first clue about Caleb’s. There was a yellow paper crown on his head, the only really homemade looking item, as the rest looked like regular clothes albeit ones in a style Essek had never seen Caleb wear before. It was a matching jacket and trouser combination in light blue with lace cuffs and an oversized white collar. There was a belt with a scabbard, although there seemed to be a wooden sword in there instead.

“No clue. Are you from the same book as Veth? Are you her footman, or butler, or something?”

Caleb tapped his nose. “It is from a book, one point for you.”

Beau groaned. “Why did you have to pick another book character? There’s no way we’ve read as much as you have Caleb, this is unfair.”

He just kept smiling. “I am sure you all own this book, but if you have read it? That depends on what you usually do with what is given to you.”

“‘ _What is given_ ’? What kind of cryptic...” Beau looked flabbergasted. 

“Oh. Oh!” Jester was hopping up and down. “Ohmygosh I should have recognized you, that book was driving me nuts every time I saw it because I couldn’t understand it, and really Caleb you should have more books in Common for us, but I remember the cover!”

Beau turned to her. “What are you talking about?” Then recognition dawned on her face. “The book from our rooms in the Tower!”

Caleb nodded, encouraging this line of thought.

“We all have a copy and you totally are dressed like the kid on the cover! It's uh, uh…?” Jester looked desperately at Beau and Fjord who shrugged. “I can’t remember the title! Something about cats or cat paw prints, but with a ‘k’...”

“Ah, close enough.” Caleb gave a little half bow. “I am der katzenprinz for the evening.”

“The cat prince.” Essek translated automatically. And then he started to flush as the group looked at him in surprise. He hadn’t meant to let that slip so easily. 

“That is correct.” Caleb looked at him curiously. “Have you been learning Zemnian?”

“Well, I thought it best to brush up on the languages of the Empire. I learned from my dealings with the Assembly that it is always good to know what people may say when they think you do not understand.” Essek was talking much too fast and his lie was shaky at best, but he really did not want to admit to this crowd that he had been teaching himself Zemnian for a completely non-political reason.

“Really?” Jester’s smile was competing with the sparkle of her tiara. “Wow Essek, what a totally wise and normal thing to do. Learning Zemnian.”

Essek felt he might melt away right where he stood. Certainly becoming a puddle would be easier than dealing with her teasing. 

“If you’re a cat prince, where’s your tail?” Fjord asked. Essek silently thanked him for changing the subject.

“No, der katzenprinz isn’t a cat who is also a prince-” Caleb started.

“Thank you for bringing that up, I had that same question.” Caduceus said. “Are you a prince that likes to dress up like a cat? Or maybe you adopted a bunch of royal cats?”

“That’s not, well, there are cats in the story but it’s not like that.” Caleb looked around at his friends. “None of you have read it? I put a copy in all of your rooms.”

It was evident from their blank faces that not a single person had read it. He sighed, but not in an unhappy way.

Beau patted his shoulder. “We’ll do a read-a-long or something the next time we’re in the tower.”

“At least your costume is super good! And it's recognizable, so the cat prince gets one point from me!” Jester did a big curtsy with her gown and outstretched her hand.

Caleb mimicked picking up the point from her open palm. “Ah, thank you Jester. Should we be keeping track of these points?”

“Wait, is this contest actually that serious?” Fjord looked a little sheepish now. “Shit, maybe I should go dig in my closet and see if I can find something better.”

Jester’s hand shot right up. “Me, me! I have a crazy good idea Fjord! Let me help!”

“Hey, that’s cheating!” Veth said. “The contest creator can’t also help the contestants!”

“But I already helped Essek! And he looks super good, it wouldn’t be nice to not let Bat Essek compete!” 

Essek jumped at the opportunity to be able to quietly spend the rest of this evening not swept up into these extroverted antics. “I am willing to disqualify myself if it would be more fair-”

“My vote goes to Essek.” Caleb spoke suddenly. “I agree with Queen Lavorre, he looks...good, like you say.” 

The benefit of dark vision meant that even in the dim evening light Essek could definitely see that Caleb’s cheeks were a little pink.

“Okay, one vote to Essek already!” Jester grinned. “He can’t be disqualified, and now he’s technically winning!”

“Wait, if we’re voting already, I vote for myself. So I guess that means me and you are tied right now.” Beau smiled at him, and while it appeared friendly Essek felt like suddenly this competition had grown very heated. 

“Can Luc vote? Is he old enough?” Veth looked like she was planning something.

“If you’re getting your kid to vote for you, I’m gonna need more votes to win. Hey, Yasha!” Beau walked off to where Yasha and the tiefling had been sitting.

Jester had a flustered expression as she looked around her friends. “Um, I guess Yeza can vote and maybe Luc too, but you can’t tell your family to vote for you just because. They need to vote honestly from their heart! And Beau: no bribes!” Beau gave a noncommittal hand wave from over her shoulder. 

“I’m gonna go change.” Fjord turned around, mumbling something about ‘ _does that shirt go with those pants?_ ’ to himself as he went.

“I gotta go help him.” Jester started to skip after him and called out behind her. “Have fun, there’s a ton of snacks and drinks, I’ll be right back!”

Essek was left standing next to Caleb and Caduceus, feeling like a whirlwind had swept in and back out in the space of a few minutes. He turned to them.

“So…” Essek grabbed at the first small-talk topic he could conjure. “It is a nice evening.”

“It’s a little cold, but the tree and the lights produce more warmth than other backyards in this city.” Caduceus said.

“Oh, yes. I have noticed that.” And just like that Essek felt he had run out of small talk already.

“Would you like a drink?” Caleb asked.

“Please.” Essek responded gratefully. He wanted something to do with his mouth other than talk.

Caleb gestured and Essek followed him over to the wine barrels on the ground. With a little wrestling and strategic tilting from them both, they eventually had two very full glasses of wine before them. 

Essek took a long sip from his glass. Caleb took a drink from his own. And they stood in silence looking at the shimmering lights in the tree branches for a long while, until their glasses were almost empty.

“I am glad you came.” Caleb interrupted the comfortable silence.

Essek didn’t mind. “I am glad too.”

“Are you?” Caleb gave him a wry smile. 

Essek laughed. “After my initial discomfort, yes, I am glad to be here now.” His smile lingered as he held eye contact with Caleb.

Caleb reached out, running a finger across the strap on Essek’s harness. “You know this reminds me, terrible as it is in this moment, of that harness I wore when we first arrived in Rosohna. That was a poor disguise, looking back on it now.”

“I admit it does remind me of you, but instead it is like your clever book harness. Practical, but attractive.”

The brief surprise on Caleb’s face melted into a warm smile. “You always think so highly of me, Essek.”

Maybe it was the wine, but Essek felt bold. “Caleb, I must ask.” He stepped back to gesture down at himself. “Do you truly think Jester picked correctly? Apparently her first instinct was a cat.”

Caleb gave him a slow look-over and Essek could feel another blush threatening. “A cat would be a traditional Halloween choice. But this...” Caleb seemed to realize how long he had been staring and shook his head a little. “It is different for you, but you wear it well.”

“Hmm.” Essek sighed and tried again. “You must know I was fishing for a better compliment than that. Do you know how uncomfortable these wings are?” He turned around, wiggling his shoulders to make them flap again. “Or how hot this layer of velvet feels compared to my usual clothes?” Yes, it was definitely the wine lending temporary strength. 

Caleb raised an eyebrow, a playful smile dancing on his lips. “Oh, if it is a compliment you are looking for... Certainly you know you always look good, you take such care with your appearance, but tonight you are making it quite difficult to focus on anyone or anything else. I cannot take my eyes off of you.” 

Essek swallowed hard and slowly turned around to face Caleb again. Well, he hadn’t expected _that_ but it seemed he might owe Jester an apology. 

Caleb’s smile dropped suddenly. “Oh. I didn’t mean to make you uncomfortable, I had assumed...I felt that you and I have been dancing for quite some time, around each other, and I thought… Forgive me, I have overstepped.”

“No, no,” Essek quickly regained his composure. “You misunderstood my silence, I wasn’t expecting… Do you mean that?”

“That you caught my eye and have it still?” The smile returned to Caleb’s face, warm but a little hesitant. “You have my attention, Essek, in this room or the next.”

It was only a manner of time before their circle of well intentioned but teasing friends returned to resume the contest. Essek’s brain started whirring into action. “Would you like to take a walk?”

Caleb glanced out past the fence and down at his outfit. “Er, perhaps we can find a private place to go? I do not think anyone outside of this party will understand our costumes.”

Essek had almost briefly forgotten that there was a world outside of this moment. “Ah, yes. Perhaps we can view your tree a little closer?”

“A fine idea.” Caleb held his hand out. Essek smiled and took it.

  
  


When Jester returned, a newly costumed Fjord right behind her, she called out to gather her friends around to do another vote. Most everyone walked back over to her, but they were missing two from their ranks.

If Jester could see a prince and a bat behind a tree, their bodies clearly entangled with one another even as they leaned out of sight, she didn’t say anything to the group.

Although privately, she was very glad to not lose her bet or lose her crown tonight.

**Author's Note:**

> Sorry for the camera panning away before they kiss, haha. But it's true to the prompt that nobody sees a thing ;)
> 
> Maybe I'll do a follow up if there's interest. This party certainly has more chaos left to describe....
> 
> Thank you all for every kudos, comment, and for reading! Happy halloween everyone!
> 
> (As always, feel free to follow me on [tumblr](https://caleb-says-nein.tumblr.com/) for more critrole shenanigans, or to prompt me with more fic to write!)


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